1. Field of the Invention
The present invention relates to a cooling agent comprising (3S)-1-menthyl 3-hydroxybutyrate, a sensate composition comprising (3S)-1-menthyl 3-hydroxybutyrate, and a production method of (3S)-1-menthyl 3-hydroxybutyrate. In addition, the invention relates to a flavor or fragrance composition, food or drink, fragrance or cosmetic, daily necessities and household goods, oral composition or pharmaceutical, which comprises the (3S)-1-menthyl 3-hydroxybutyrate or sensate composition.
2. Description of the Related Art
Up to now, cooling agents which exert a refreshing sense (refresh-feeling) or cool sense (cool-feeling), namely cooling effect, on human skin, oral cavity, nose and throat are used in dentifrices, sweets (e.g., chewing gum, candy and the like), tobacco, poultice, cosmetics and the like. As a flavoring substance which provides such a refresh-feeling or cool-feeling, 1-menthol (1-menthol) is now broadly used but its cooling effect has a weak point of lacking in persistency and its using concentration and application being limited because it has peculiar bad smell, bitter taste and the like.
In addition to 1-menthol, a large number of compounds have been proposed and also used as the compound having cooling effect. In exemplifying the so far proposed compounds having cool-feeling effect other than 1-menthol, for example, 3-substituted-p-menthane (e.g., see JP-A-47-16647), N-substituted-p-menthane-3-carboxamide (e.g., see JP-A-47-16648), 1-menthyl glucoside (e.g., see JP-A-48-33069), 3-(1-menthoxy)propane-1,2-diol (e.g., see JP-A-58-88334), 1-menthyl 3-hydroxybutyrate (e.g., see JP-A-61-194049), 1-alkoxy-3-(1-menthoxy)propane-2-ol (e.g., see JP-A-2-290827), esters of 3-hydroxymethyl-p-menthane (e.g., see JP-A-5-255186), N-acetylglycinementhane methyl ester (e.g., see JP-A-5-255217), (−)-isopulegol (e.g., see JP-A-6-65023), (2S)-3-(1-menthoxy)propane-1,2-diol (e.g., see JP-A-7-82200), 2-hydroxymethylmenthol (e.g., see JP-A-7-118119) and the like can be mentioned.
In some cases of the above-mentioned compounds having cooling effect, it is necessary to avoid their use or limit their using amount, because a strong bitterness is felt as the sense of taste when they are used in flavors or the like, for example when used in chewing gum, candies and the like or oral hygiene goods such as dentifrice and mouth wash.